CA1159071A - Oxime carbamates et oxime carbonates, agents de protection pour les cultures - Google Patents

Oxime carbamates et oxime carbonates, agents de protection pour les cultures

Info

Publication number: CA1159071A
Authority: CA; Canada
Prior art keywords: compound; formula; decomp; imino; benzacetonitrile
Prior art date: 1978-08-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000310206A

Other languages

English (en)

Inventor

Henry Martin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-08-31

Filing date

1978-08-29

Publication date

1983-12-20

1978-08-29 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1983-12-20 Application granted granted Critical

1983-12-20 Publication of CA1159071A publication Critical patent/CA1159071A/fr

Status Expired legal-status Critical Current

Links

-1 Oxime carbamates Chemical class 0.000 title claims abstract description 27
230000004224 protection Effects 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 55
239000003905 agrochemical Substances 0.000 claims abstract description 9
230000009931 harmful effect Effects 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical group 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
229910052717 sulfur Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 claims 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
239000000729 antidote Substances 0.000 abstract description 46
239000004009 herbicide Substances 0.000 abstract description 22
229940075522 antidotes Drugs 0.000 abstract description 6
238000007654 immersion Methods 0.000 abstract description 3
239000006185 dispersion Substances 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 85
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239000013543 active substance Substances 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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239000012467 final product Substances 0.000 description 6
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
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WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
240000005979 Hordeum vulgare Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000428 dust Substances 0.000 description 3
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239000010695 polyglycol Substances 0.000 description 3
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
BWRPEDIXOHZKFD-UHFFFAOYSA-N 2,2-diphenoxyacetic acid Chemical class C=1C=CC=CC=1OC(C(=O)O)OC1=CC=CC=C1 BWRPEDIXOHZKFD-UHFFFAOYSA-N 0.000 description 2
HKROQOWBHZLRCU-UHFFFAOYSA-N 2,2-diphenoxypropanoic acid Chemical class C=1C=CC=CC=1OC(C(O)=O)(C)OC1=CC=CC=C1 HKROQOWBHZLRCU-UHFFFAOYSA-N 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
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150000002500 ions Chemical class 0.000 description 2
235000019713 millet Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
SCCDDNKJYDZXMM-UHFFFAOYSA-N dimethachlor Chemical compound COCCN(C(=O)CCl)C1=C(C)C=CC=C1C SCCDDNKJYDZXMM-UHFFFAOYSA-N 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
DNKFFWHBZNMRBA-UHFFFAOYSA-N ethyl 2-cyano-n-hydroxyethanimidate Chemical compound CCOC(=NO)CC#N DNKFFWHBZNMRBA-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000003966 growth inhibitor Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000001469 hydantoins Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
239000011785 micronutrient Substances 0.000 description 1
235000013369 micronutrients Nutrition 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000012856 packing Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BHLUERUPCAAQGF-UHFFFAOYSA-N prop-2-yne-1-thiol Chemical compound SCC#C BHLUERUPCAAQGF-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Toxicology (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Furan Compounds (AREA)

CA000310206A 1978-08-31 1978-08-29 Oxime carbamates et oxime carbonates, agents de protection pour les cultures Expired CA1159071A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7835200A GB2028797B (en)	1978-08-31	1978-08-31	Oxime carbamates and oxime carbonates for the protection of cultivatec crops

Publications (1)

Publication Number	Publication Date
CA1159071A true CA1159071A (fr)	1983-12-20

Family

ID=10499379

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000310206A Expired CA1159071A (fr)	1978-08-31	1978-08-29	Oxime carbamates et oxime carbonates, agents de protection pour les cultures

Country Status (11)

Country	Link
JP (1)	JPS5535002A (fr)
AT (1)	AT365410B (fr)
AU (1)	AU530210B2 (fr)
BE (1)	BE870066A (fr)
CA (1)	CA1159071A (fr)
DE (1)	DE2837204A1 (fr)
FR (1)	FR2434802A1 (fr)
GB (1)	GB2028797B (fr)
LU (1)	LU80165A1 (fr)
NL (1)	NL7808962A (fr)
SE (1)	SE446926B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE870067A (fr) *	1978-09-04	1979-02-28	Ciba Geigy	Derives d'oximes pour la protection des cultures
DE3041998A1 (de)	1980-11-07	1982-06-09	Bayer Ag, 5090 Leverkusen	Pyrazolsubstituierte oximino-cyan-acetamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
US4566901A (en) *	1982-05-06	1986-01-28	Ciba-Geigy Corporation	Novel oxime ethers, the preparation thereof, compositions containing them and the use thereof
EP0144283A1 (fr) *	1983-10-04	1985-06-12	Ciba-Geigy Ag	Agents herbicides
US4640927A (en) *	1984-03-30	1987-02-03	Uniroyal Chemical Company, Inc.	Substituted oxime carbamates
GB2173791B (en) *	1985-04-16	1989-07-05	Ici Plc	Fungicidal cyano oximes
WO1991016299A1 (fr) *	1989-04-25	1991-10-31	E.I. Du Pont De Nemours And Company	Carbamates d'oxime fongicides
IL94170A0 (en) *	1989-04-25	1991-01-31	Du Pont	Oxime carbamates and their use as fungicides
DE19622354A1 (de) *	1996-06-04	1997-12-11	Bayer Ag	Halogenthiophen-Derivate
SG77689A1 (en) *	1998-06-26	2001-01-16	Ciba Sc Holding Ag	New o-acyloxime photoinitiators
EP0980863B1 (fr) *	1998-08-17	2005-02-02	Givaudan SA	Dérivés d'acides oximinocarboxyliques
DE69923505T2 (de) *	1998-08-17	2006-01-12	Givaudan S.A.	Oximcarbonsäure Derivate
US7071211B2 (en) *	2002-09-27	2006-07-04	Bausch & Lomb Inc.	Small organic molecules that increase the activity of gelatinase a in ocular cells
CA2679741A1 (fr) *	2007-03-15	2008-09-18	Sun Pharma Advanced Research Company Ltd.	Nouveaux promedicaments
EP2486797A1 (fr) *	2011-07-28	2012-08-15	Bayer CropScience AG	Utilisation de matières actives de traitement de semences issues du groupe des insecticides à base de carbamates en tant que phytoprotecteur pour des herbicides oxadiazolones
CN110563869B (zh) *	2019-09-05	2021-05-11	苏州昊帆生物股份有限公司	一种树脂型多肽缩合试剂及其制备方法与应用

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL224194A (fr) *	1957-01-21
NL282623A (fr) *	1961-09-01
NL302370A (fr) *	1962-12-22
GB1063363A (en) *	1963-03-14	1967-03-30	African Explosives & Chem	Improvements in or relating to insecticidal compounds of the phenyl or naphthyl carbamoyl oxime type
DE1221840B (de) *	1963-09-21	1966-07-28	Bayer Ag	Mittel zur Bekaempfung von Wasserunkraeutern
DE1232947B (de) *	1963-12-09	1967-01-26	Fahlberg List Chemische Veb	Verfahren zur Herstellung von Ketoximcarbanilaten aus Ketoximen und Arylisocyanaten
GB1138057A (en) *	1966-10-11	1968-12-27	Shell Int Research	Carbamoyl oxime derivatives
FR1498899A (fr) *	1965-11-10	1968-01-10	Shell Nv
FR1542325A (fr) *	1966-11-10	1968-10-11	Ciba Geigy	Nouveaux agents pesticides
US3483246A (en) *	1966-12-05	1969-12-09	Mobil Oil Corp	Aromatic glyoxynitrile oximino carbanates
US3575972A (en) *	1966-12-05	1971-04-20	Mobil Oil Corp	Morpholino carbonyl glyoxylonitrile oximino dialkyl carbamates
US3621049A (en) *	1969-04-01	1971-11-16	American Cyanamid Co	Cyanoalkylaldoxime carbamates
FR2097552A5 (fr) *	1970-07-10	1972-03-03	Roussel Uclaf
DE2120087A1 (en) *	1971-04-24	1972-11-09	Farbenfabriken Bayer Ag, 5090 Leverkusen	Selective-herbicidal nitrobenzaldoxime carbamates - - for weed control in root crop culture
ZA731111B (en) *	1972-03-15	1974-03-27	Du Pont	2-cyano-2-hydroxyiminoacetamides and acetates as plant disease control agents
FR2202689B1 (fr) *	1972-10-17	1975-10-31	Delalande Sa
US3890135A (en) *	1973-01-18	1975-06-17	Du Pont	Trifluoromethylbenzophenone O-acyloximes and their use as crop yield increasers for plants
JPS49133354A (fr) *	1973-04-26	1974-12-21
US3901683A (en) *	1973-07-23	1975-08-26	Diamond Shamrock Corp	Crop yields with ketoximes
DE2436654A1 (de) *	1973-08-02	1975-02-20	Ciba Geigy Ag	Oximinocyanacetamid-derivate
JPS6051460B2 (ja) *	1975-04-22	1985-11-14	藤沢薬品工業株式会社	炭酸エステル類、その製造方法およびその用途
DE2517653A1 (de) *	1975-04-22	1976-11-25	Bayer Ag	Carbamoyl-oxime, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
CH624552A5 (fr) *	1975-09-04	1981-08-14	Ciba Geigy Ag
DE2616481A1 (de) *	1976-04-14	1977-11-03	Merck Patent Gmbh	Bis-quartaere pyridinium-2-aldoxim- salze und verfahren zu ihrer herstellung
DE2626828A1 (de) *	1976-06-15	1977-12-22	Bayer Ag	Neue carbamidsaeureoximester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
CH632130A5 (en) *	1977-03-02	1982-09-30	Ciba Geigy Ag	Compositions on the basis of oxime ethers, oxime esters or oxime carbamates which are suitable in agriculture for crop protection

1978
- 1978-08-18 AT AT0601378A patent/AT365410B/de not_active IP Right Cessation
- 1978-08-23 SE SE7808906A patent/SE446926B/xx not_active IP Right Cessation
- 1978-08-25 DE DE19782837204 patent/DE2837204A1/de active Granted
- 1978-08-28 LU LU80165A patent/LU80165A1/de unknown
- 1978-08-29 CA CA000310206A patent/CA1159071A/fr not_active Expired
- 1978-08-30 FR FR7825043A patent/FR2434802A1/fr active Granted
- 1978-08-30 BE BE190145A patent/BE870066A/fr not_active IP Right Cessation
- 1978-08-30 AU AU39380/78A patent/AU530210B2/en not_active Expired
- 1978-08-31 NL NL7808962A patent/NL7808962A/nl not_active Application Discontinuation
- 1978-08-31 JP JP10697378A patent/JPS5535002A/ja active Pending
- 1978-08-31 GB GB7835200A patent/GB2028797B/en not_active Expired

Also Published As

Publication number	Publication date
NL7808962A (nl)	1980-03-04
GB2028797A (en)	1980-03-12
GB2028797B (en)	1983-04-27
SE7808906L (sv)	1980-02-24
ATA601378A (de)	1981-06-15
FR2434802B1 (fr)	1981-03-06
BE870066A (fr)	1979-02-28
SE446926B (sv)	1986-10-20
LU80165A1 (de)	1979-05-15
JPS5535002A (en)	1980-03-11
AU3938078A (en)	1980-03-06
AU530210B2 (en)	1983-07-07
DE2837204A1 (de)	1980-03-06
AT365410B (de)	1982-01-11
FR2434802A1 (fr)	1980-03-28

Legal Events

Date	Code	Title	Description
2000-12-20	MKEX	Expiry

Publication	Publication Date	Title
US4415743A (en)	1983-11-15	Furanyl oximes
CA1149398A (fr)	1983-07-05	Compositions a base d'ether-oximes et d'ester-oximes stimulant la croissance des plantes et protegeant celles-ci
CA1164869A (fr)	1984-04-03	Agents pour proteger les cultures
CA1159071A (fr)	1983-12-20	Oxime carbamates et oxime carbonates, agents de protection pour les cultures
US4220464A (en)	1980-09-02	Phenylglyoxylonitrile-2-oxime-cyanomethyl ether as plant growth regulator
JPH0672131B2 (ja)	1994-09-14	オキシムエ−テル、その製造方法、該化合物を含有する栽培植物保護用組成物および栽培植物保護方法
CA1161452A (fr)	1984-01-31	Oximes sulfures, procedes pour les fabriquer, et leur empoi pour la protection des cultures
US4500347A (en)	1985-02-19	Oxime derivatives for protecting plant crops
GB2029223A (en)	1980-03-19	Oxime derivatives for the protection of cultivated crops
US4439228A (en)	1984-03-27	Oxime derivatives for protecting plant crops
US4453974A (en)	1984-06-12	Phenyl- and naphthyl-glyoxylonitrile oximino carbamates for the protection of crops against injury by herbicides
US4416686A (en)	1983-11-22	3,4-Dichlorophenylacetonitrile-N-tert.butylcarbamoyloxy ether for the protection of crops against injury by herbicides
JPS5838422B2 (ja)	1983-08-23	置換シクロプロピルメトキシアニライド及び除草組成物
US4475945A (en)	1984-10-09	Aminoglyoxyloitrile oximino carboxylic acid esters and thio esters for the protection of crops against injury by herbicides
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US4426221A (en)	1984-01-17	Oxime carbamates for the protection of cultivated crops
US4453969A (en)	1984-06-12	Thienylglyoxylonitrile oximino phenylcarbamates for the protection of crops against injury by herbicides
US4532732A (en)	1985-08-06	Oxime derivatives for protecting plant crops
US4581060A (en)	1986-04-08	Compositions, which promote plant growth and protect plants, based on oxime ethers and oxime esters
US4497648A (en)	1985-02-05	Oxime derivatives for protecting plant crops
IE47319B1 (en)	1984-02-22	Oxime carbamates and oxime carbonates for the protection of cultivated crops
CA1205475A (fr)	1986-06-03	Derives de 1,3-thiazolidine
CA1130312A (fr)	1982-08-24	Derives d'oximes pour la protection des recoltes
CS207722B2 (cs)	1981-08-31	Prostředky k ochraně kulturních rostlin před agresivními agrochemikáliemi